1: With water; lithium hydroxide hydrate in methanol T=0 - 20°C; 0.5 h; 2: With potassium hydrogensulfate; water in methanol

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '21162132', constants.ctx, '0')">palladium on carbon</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587189', constants.ctx, '0')">hydrogen</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098229', constants.ctx, '0')">methanol</a> <br /> <br /> &nbsp;

<b>Multi-step reaction with 8 steps<br /> </b>1: 1) SOCl₂ / 1) CH₂Cl₂, -25 degC, 10 min, 2) CH₂Cl₂, -20 degC, 2 h<br />2: LDA / tetrahydrofuran; hexane / 0.5 h / -80 &deg;C<br />3: 90 percent / H₂, DMAP, 1N aq.KHCO₃ / 5percent Pd-C / dioxane / 5 h / 825.07 Torr / Ambient temperature<br />4: 98 percent / H₂ / PtO₂ / ethyl acetate / 24 h / 22501.8 Torr<br />5: 98 percent / DMAP / tetrahydrofuran / 24 h / Ambient temperature<br />6: 93 percent / CsCO₃ / methanol / 40 h / Ambient temperature<br />7: 88 percent / H₂, Et₃N / Pd-C / ethanol / 16 h / 3375.3 Torr / Ambient temperature<br />8: 1) 1 N NaOH / 1) THF, r.t., 2 h<br /> <br /> &nbsp;